Bed and breakfast vacation rentals in Oak Bluffs

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Top-rated bed and breakfast rentals in Oak Bluffs

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Guest favorite

A spacious screened porch features comfortable seating on wrought iron furniture with floral cushions. A small round table is set against the wall, while a flat surface transitions to a wooden deck visible through large screens. Soft natural light filters through the space.

Private room in North Falmouth

4.81 out of 5 average rating, 644 reviews

Cape Cod Cottage

The space is available for one to four guests in the same party. Accommodations are in a separate wing of the house. There are two bedrooms, one with a double bed and one with twin beds. There is a private bath as well as a sitting room and screen porch for the exclusive use of the guest. The house is within walking distance to a private ocean beach and within a mile of the Shinning Sea Bike Path (bike rentals are available nearby). Numerous restaurants serving traditional Cape fare are within a two mile radius, with many more in nearby Falmouth and Woods Hole. Breakfast is provided.

Superhost

Two wooden adirondack chairs are positioned in a sandy corner, surrounded by a wooden fence and tall greenery. A potted plant with red flowers sits on a small table between the chairs, creating a peaceful outdoor seating area.

Private room in Oak Bluffs

4.88 out of 5 average rating, 72 reviews

Oak Bluffs/In Town/ Harbor Views/ Queen Bed

Welcome to Watchaboat! Our family home has a comfortable, clean room available. The room has a beachy cottage feel where you'll be happy to rest at the end of a summer day. We've got a great location, overlooking Oak Bluffs harbor, a 9-minute walk to downtown OB & a quick stroll to Oak Bluffs Town Beach (.3 mile). Our bustling home has a busy business on the property, so it's fit for travelers who need to drop their bags & go enjoy the island. Please read the listing carefully before booking!

Lush greenery surrounds the historic inn, featuring mature trees and vibrant shrubs. The garden area showcases well-maintained plants, creating a serene outdoor space. The white exterior of the inn is visible in the background, harmonizing with the natural landscape.

Private room in Fairhaven

4.97 out of 5 average rating, 30 reviews

Warren Delano Room at the Delano Homestead B&B

Comfortable, historic inn located in the village center of a classic seaport. Walk to restaurants, fishing piers, bike path, beach, shopping. Short drive to museums, ferries, beaches, cape, Newport, Boston, etc. Breakfast included. One large room with a king-sized bed and private bath. The bath is a few feet away in private area and we provide robes. But, if you want two rooms and are comfortable sharing the bath, please let us know and we can give you a price for two rooms with shared bath.

Top guest favorite

Private room in North Falmouth

4.91 out of 5 average rating, 235 reviews

North Falmouth Suite 'downstairs suite'

This gueen-bed suite has a private entrance, a living room with wifi/tv, and a small, private bath, on a beautifully maintained property on 28A in N. Falmouth. Enjoy easy access to beaches & the bike path is across the street. The suite is priced based on two people, additional people - older kids, friends, are $40/night more; two twin blow-ups can be set up in living room. You must list the total amount of guests when booking. This house is not well suited to toddlers & young children.

The entrance of Kathleen's Kottage is surrounded by verdant greenery and colorful flower arrangements. A well-maintained gravel pathway leads to a welcoming porch, featuring white railings and potted plants. The cottage displays a charming shingle exterior, highlighting the friendly character of the residence.

Private room in Oak Bluffs

5 out of 5 average rating, 26 reviews

The Mary Suite - in Oak Bluffs MV

Kathleen Nasser is the owner of Kathleen's Kottage, a seasonal Host Home located in Oak Bluffs, MA. This is the Mary Suite the most private and spacious room. The suite is located on the second floor of the building adjacent to the main house. The suite has a private entrance with a lockable door. King size bed. Private bath with dual sinks. Sitting room. Cable TV, AC and Internet. Microwave, Refrigerator and Coffeemaker. Serving a light fare breakfast. We are small Pet Friendly.*

Superhost

A bright guest room features a spacious bed adorned with a textured white coverlet. Large windows invite ample natural light, complemented by a cozy window seat with decorative pillows. Floral accents enhance the room's charm. Warm tones and traditional decor create a welcoming atmosphere.

Private room in Barnstable

4.91 out of 5 average rating, 90 reviews

Retreat to Cape Cod Home on Water

Private home built in 1906. Two lovely guest rooms in an ideally Cape Cod home overlooking Nantucket Sound and the Centerville and Bumps rivers. Both rooms have window seats and provide a traditional New England style. You will love the proximity to the ferries, P-Town, Woods Hole, great beaches, lakes, restaurants, theaters, shopping and whale watching. Both rooms have AC. Sorry to say, but my listing is not suitable for children under the age of 12; because of stairs and dock.

Guest favorite

A welcoming entryway features a pair of patterned chairs around a small table. A potted plant adds a touch of greenery. Natural light filters through a window decorated with lace curtains, illuminating the tiled floor and wooden door.

Private room in Pocasset

4.93 out of 5 average rating, 225 reviews

Cape Cod/Bourne: Cape Escape Suite

Quiet, fully Private suite in my non-smoking, post and beam home. A sitting area with light cooking access available. Private entrance and bath. Wood floors throughout. Guests say the space is larger than photos reveal. Hiking trails and quiet cove with beautiful sunsets are a 5 min walk away. Close to Bike path to Woods Hole and along the canal. Cape Flyer stop near by. A Pick up is available. Recommend a 3 night stay in order to fully explore the Cape and an island.

Top guest favorite

A welcoming front porch is lined with columns and features hanging flower pots. Comfortable seating arrangements are provided, including chairs and a small table. Lush greenery surrounds the porch, enhancing the inviting outdoor space.

Private room in Falmouth

4.96 out of 5 average rating, 244 reviews

Secret Garden Suite with full breakfast

We built our home in 1997 and have shared it with our five children, grandchildren and extended family. We thought someday when the kids leave, we will make it into a Bed & Breakfast and Airbnb has made the dream simply possible. Joining Airbnb in May 2016 changed and enriched our lives by the many travelers we have hosted and friends we have made. We look forward to being your host soon. We believe that the breakfast we include with the room rate adds substantial value .

A well-maintained garden is visible beside a shingled exterior of the property. Rounded shrubs and vibrant flowers add color and texture. Steps lead up to an entrance accented by lush greenery, providing a welcoming transition into the home.

Private room in West Tisbury

4.89 out of 5 average rating, 27 reviews

Bright, Unique on Martha's Vineyard!

SPRING SPECIAL through June 15: Min Stay 2 nights, stay third night, get 30% rebate from hostess! A spacious room with bath in a studio behind my house, opens onto a broad meadow, abuts bike & walking trails. Serene, yet just 5-20 minutes from beaches & towns & all the lively Island happenings. If you are coming for a wedding, an anniversary, a reunion or just for the humming of nature and the sea, The Broad Meadow is for you. NO ROOM TAX - Good breakfast & beach passes!

Guest favorite

A welcoming front porch is shown, featuring a series of wooden rocking chairs positioned against a backdrop of shingled siding. The stairs lead down to a well-manicured yard with newly planted flowering shrubs, framed by a neatly covered foundation.

Private room in West Tisbury

4.96 out of 5 average rating, 28 reviews

warm and spacious B and B in our Martha's Vin home

Quintessential vineyard beach house set among woods, farms, and wildlife sanctuaries. This recently built, sunny West Tisbury B and B is minutes away from beaches, including coveted Lambert's Cove beach. Sink into a comfy queen bed after a day of fun, and enjoy private bath, laundry room and separate entrance. Awake to singing birds, then explore our island after starting your day with steaming coffee/tea and pastries which can be enjoyed on the spacious front porch.

Guest favorite

The exterior of the post and beam structure features a wraparound porch adorned with flower boxes and views of the surrounding greenery. A fenced yard is visible, complemented by a grassy lawn and mature trees, creating a serene outdoor space.

Private room in Tisbury

4.96 out of 5 average rating, 129 reviews

Spacious 1850s rustic meets modern walkout studio

Located on 1.6 acres, just a 6 minute drive from Vineyard Haven town center, this lovely post and beam walk out basement apartment is the perfect home base to explore the island. Although the home was built in 2000 and has all the modern amenities you could hope for, its structure, reclaimed from a Connecticut dairy barn built in 1852 brings old world charm to this stunning space. Please note that our family of 5 lives upstairs so there is potential for noise.

Guest favorite

A tranquil garden area features relaxing lawn chairs positioned on lush green grass. The entrance of the Inn is visible, framed by vibrant flowers and foliage. A rustic wooden table is set nearby, enhancing the serene outdoor setting.

Private room in Vineyard Haven

4.88 out of 5 average rating, 51 reviews

The Look Inn/Parrish Room

The Look Inn is a licensed bed and breakfast Inn by the Town of Tisbury/Vineyard Haven celebrating our 30th year of operation. The Parrish and Blue and Look Out Rooms have a queen size bed and can sleep one or two people. The rooms shares a full bath with the rooms that each have sinks with hot/cold water and the common spaces of living room with tv and screened porch. There are relaxing lawn chairs that view the many gardens of flowers and vegetables.